Pics Of Kimberly Guilfoyle That Make Us Miss Her Pre-Plastic Surgery Face

Kimberly Guilfoyle has not only undergone a complete style transformation over the past two decades, but her makeup style has also drastically changed. While this usually results in more sophisticated and refined looks for most people, the opposite is true for Donald Trump Jr.'s ex-fiancée, who continues to make fashion and makeup mistakes that she should have long ditched. However, it wasn't just her outfit and beauty choices that took a wrong turn after she joined the MAGA-sphere and began dating Donald Jr. in 2018.

For years now, Guilfoyle has been dogged by plastic surgery rumors that only grow worse each time she shares a photo from her pre-Trump days. In June 2025, an innocent birthday tribute on Instagram Story featuring a throwback photo of her old face put her rumored plastic surgery on blast. She also had social media users doing a double-take in 2015 due to her unrecognizable look in old pics from her days as a fashion and lingerie model in the '80s and '90s.

While she's never copped to going under the knife for facial tweaks, some experts believe that several changes in Guilfoyle's appearance can be attributed to cosmetic work. "I think initially [Guilfoyle] started out with Botox to her forehead, crow's feet around her eyes, and glabella area, as well as good skin care. I believe over time she has continued to add to this, using fillers in an effort to improve bone structure and maintain the youthful, desired inverted-triangle appearance from her mid-face to her chin," Dr. Dennis Schimpf, a South Carolina-based board-certified plastic surgeon, told Glam.

For those who want to see what the former Fox News host looked like before her dramatic transformation, check out these photos of Kimberly Guilfoyle that make us miss her pre-plastic surgery face.

Kimberly Guilfoyle looked like she could have easily joined the cast of the iconic teen supernatural movie "The Craft" and played a sexy and mysterious young witch in this photo of her and her then-husband Gavin Newsom posing for the camera alongside fellow attendees at the 22nd Annual Napa Valley Wine Auction in California in 2002. At the time, Guilfoyle was still working as an assistant district attorney and prosecutor for the San Francisco District Attorney's Office and appeared to have yet to discover Botox.

The year 2004 marked a career shift for Kimberly Guilfoyle, transforming from prosecutor to television host. She began to host Court TV's "Both Sides" and served as a legal commentator on programs such as "Good Morning America" and "Anderson Cooper 360." Though she had already put her modeling days behind her, this didn't stop Guilfoyle from looking like a Victoria's Secret model at a gala in New York City. This shouldn't come as a surprise, however, as she previously modeled lingerie for the fashion brand.

Before she became one of Donald Trump's most loyal supporters, Kimberly Guilfoyle attended events like the GLAAD Media Awards. In 2004, she graced the award show's 15th iteration alongside her then-boss, Court TV CEO Henry Schleiff. A far cry from Guilfoyle's more recent looks, she gave '90s bombshell in full glam makeup, mid-length hair, and a figure-hugging little black dress. It's unclear if she took style inspiration from Monica Geller, but this look trumps (pun intended) around 90% of the fashion and makeup disasters she's been giving since 2018.

Nothing made us miss Kimberly Guilfoyle's old face and style more than her modeling-era photos, including one in which she channelled a 1940s pin-up model. Unfortunately, Guilfoyle modeled only to earn enough money to pursue her true love. "I knew I wanted to go to law school, and it ended up being a great way to pay for it. I modeled everything from clothes, swimwear, and lingerie, including Victoria's Secret! I met an incredible number of interesting people through modeling and really learned a lot about self-confidence and self-worth," she told People.

While Kimberly Guilfoyle's style during Donald Trump's third run and second term as president leans toward tacky baby doll and bodycon dresses and thick, cakey glam, she also had a cool girl era back in the day. In 2005, she attended a gathering held in honor of Jeremy Piven at a New York City bar rocking a simple black top, low-waist jeans, a black choker, multi-layer necklaces, and huge earrings. The then-prosecutor had not yet become heavy-handed with her eyeliner and foundation; instead, her simple glam beautifully showcased her stunning features.

Kimberly Guilfoyle had been the first lady of San Francisco for less than two years when her marriage to Gavin Newsom broke down in January 2005 over his infidelity. However, she appeared to have bounced back by November of that year, with photos showing her looking radiant as she attended a bash thrown by fashion designer Brian Reyes in New York City to celebrate his spring 2006 collection. In one image, Guilfoyle could be seen flashing a huge and gorgeous smile at the camera, looking effortlessly chic in a monochromatic look.

In 2009, Kimberly Guilfoyle made an appearance at a screening of the film "I Love You, Man" in New York City sporting a look reminiscent of Angelina Jolie's eyeliner-heavy makeup style in the 2000s. Like Jolie, Guilfoyle's glam highlighted her superior bone structure, giving a clear reminder that she once worked as a model. Whether or not she'd already started to dabble in plastic surgery at the time this photo was taken is unknown, but she does look like a different person from the Kimberly Guilfoyle we know today.